Isopropyl iodide → 5-Bromo-2-(1-methylethoxy)pyridine

HRID 1663599Notes

Reaction equation

HRID 1663599 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH:9](I)([CH3:11])[CH3:10]>C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Ag+2]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 6362Isopropyl iodideHCID 5995285-Bromo-2-hydroxypyridine

Product 1

HCID 219350685-Bromo-2-(1-methylethoxy)pyridineYield 97%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 5-bromo-1H-pyridin-2-one (2 g) and silver carbonate (4.3 g) in chloroform (40 mL) was added isopropyl iodide (11.5 mL) and the mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered through silica gel (20 g) and the filtrate was concentrated in vacuo. The resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=98:2→90:10) to give 5-bromo-2-isopropyloxypyridine (2.41 g, yield: 97%).

Workup

  1. filtrationThe reaction mixture was filtered through silica gel (20 g)
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=98:2→90:10)

Sources & evidence

ORD record
ord-5e4a3d0323fd40299aab7d5d979ee45a
Source dataset
uspto-grants-2011_10
Patent number
US08034949B2

Reaction notes

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